Barbara Walters and David Letterman are both nearing the end of their careers, and it seems they’re feeling reflective.

During Wednesday’s episode of The Late Show, Letterman asked Walters, his guest, what she makes of Monica Lewinsky’s resurgence. Lewinsky—who wrote a first-person essay for the June issue of Vanity Fair—says that she’s been unable to find suitable work, despite graduating from the London School of Economics. Walters said that she’s fond of Lewinsky, and quasi-revealed that there had been some discussions about having Lewinsky on The View, before backing off from making any concrete revelations.

What was revelatory, however, was Letterman’s seemingly genuine remorse at having so brutally joked about Lewinsky in the years since the 1998 scandal. “So I’m thinking . . . it’s sort of like the violence in the elevator,” Letterman said, referring to a leaked video that showed Jay Z being assaulted by Solange Knowles. “Is it funny because they’re just famous? Or overall with some perspective do you realize this is a sad human situation?” (It bears mentioning that Letterman had his own office sex scandal—the host admitted to having affairs with female staffers after an alleged blackmail plot in 2009.)

“President Clinton has been able to move on,” Walters noted. “Hillary Clinton may run for president. I wish them both well. Monica is still stuck in the humor of it, and she is an intelligent and nice woman.”

Walters remembered that Lewinsky had told her, in a 1999 interview, that she would one day tell her children, “Mommy made a big mistake.” (Lewinsky, now 40, is not a mother, and writes about the difficulties she’s had in relationships in her Vanity Fair essay.) “Let’s just say she was working at Dairy Queen—and I’m not being funny,” Letterman pondered. “But let’s just say the same thing happened at Dairy Queen, would she then tell her kids that it was a big mistake? Or would she just say, ‘Oh for God’s sake I was 22, and 22-year-olds are irresponsible’ and on and on.”

Walters said she’s never heard Monica blame the scandal on her youth. “Because that’s what a lot of us feel,” she continued. “She was just a kid. But she has had been ridiculed now for all these years.”

Letterman then offers up some remorse (“I feel bad about my role in helping push the humiliation to the point of suffocation”), to which Walters simply replies, “Good. Then we can stop.”

Walters is retiring from television at the end of this week, and Letterman is being succeeded by Colbert Report host Stephen Colbert some time in 2015.